New Isoxazole‐Substituted Aryl Iodides: Metal‐Free Synthesis, Characterization and Catalytic Activity
New Isoxazole‐Substituted Aryl Iodides: Metal‐Free Synthesis, Characterization and Catalytic Activity
复制标题
新型异恶唑取代芳基碘化物：无金属合成、表征和催化活性
DOI：
10.1002/ejoc.202301191
复制
发表时间：
2024
影响因子：
2.8
通讯作者：
Kumar, Ravi
中科院分区：
文献类型：
--
作者：
Uttam, Bhawna;Zhdankin, Viktor V.;Kumar, Ravi
通过2-碘-1,3-双(丙-2-yn-1-基氧基)苯(4)与相应的苯甲醛肟5 a-5 d的DIB介导的[3+2]环加成反应合成了一系列新的异恶唑取代的芳基碘化物1 a–1 d。通过IR、1H NMR、13C NMR和HRMS对合成的芳基碘化物1的结构进行了表征。 1 的结构也通过单晶X射线晶体学得到证实。此外，还筛选了碘芳烃1 a–1 d对氢醌和硫化物氧化的催化活性。使用芳基碘化物1和m-CPBA作为末端氧化剂进行氧化时，对苯二酚产生苯醌，而硫化物则产生相应的亚砜，收率良好至优异。碘芳烃1 b对硫化物和氢醌的氧化表现出最好的催化活性。此外，碘芳烃1 b也被用于苯乙酮的α-氧化酰化。
A series of new isoxazole‐substituted aryl iodides1 a–1 dhave been synthesized by DIB‐mediated [3+2] cycloaddition reaction of 2‐iodo‐1,3‐bis(prop‐2‐yn‐1‐yloxy) benzene (4) with corresponding benzaldehyde oximes5 a–5 d. Structure of the synthesized aryl iodides1were characterized by IR,1H NMR,13C NMR and HRMS. The structure of1 awas also confirmed by single‐crystal X‐ray crystallography. Further, catalytic activity of iodoarenes1 a–1 dwas screened for the oxidation of hydroquinones and sulfides. On oxidation using aryl iodides1withm‐CPBA as terminal oxidant, hydroquinones afforded benzoquinones while sulfides gave corresponding sulfoxides in good to excellent yields. Iodoarene1 bshowed the best catalytic activity for the oxidation of sulfides and hydroquinones. Moreover, iodoarene1 b, was also utilized for α‐oxytosylation of acetophenones.